Alogliptin Impurity 07 - ≥95% , CAS No.1618644-29-3

CAS: 1618644-29-3 Cat. No.: A943980 Summenformel: C₂₀H₁₃ClN₄O₂ Molekulargewicht: 376.8 PubChem CID: 70306796

QUALITÄT & REINHEIT ≥95%

Storage

Room temperature

Spezifikationen

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

C1=CC=C(C(=C1)CN2C(=CC(=O)N(C2=O)CC3=CC=CC=C3C#N)Cl)C#N

IUPAC Name

2-[[6-chloro-3-[(2-cyanophenyl)methyl]-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile

InChIKey

RUEYVZYCZVUXKX-UHFFFAOYSA-N

INCHI

1S/C20H13ClN4O2/c21-18-9-19(26)25(13-17-8-4-2-6-15(17)11-23)20(27)24(18)12-16-7-3-1-5-14(16)10-22/h1-9H,12-13H2

Isomere SMILES

C1=CC=C(C(=C1)CN2C(=CC(=O)N(C2=O)CC3=CC=CC=C3C#N)Cl)C#N

PubChem CID

70306796

Molekulargewicht

376.8

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Benzonitriles

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzonitriles
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzonitriles
• Alternative Parents: Pyrimidones Halopyrimidines Hydropyrimidines Aryl chlorides Vinylogous halides Vinylogous amides Heteroaromatic compounds Ureas Lactams Nitriles Azacyclic compounds Organooxygen compounds Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Benzonitrile - Halopyrimidine - Pyrimidone - Aryl chloride - Aryl halide - Hydropyrimidine - Pyrimidine - Heteroaromatic compound - Vinylogous amide - Vinylogous halide - Lactam - Urea - Azacycle - Nitrile - Carbonitrile - Organoheterocyclic compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Cyanide - Organic oxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Molekulargewicht: 376.800 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 376.073 Da
• Monoisotopic Mass: 376.073 Da
• Topological Polar Surface Area: 88.200 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 731.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No assay application protocols (WB, IHC, IF, FC) apply to this chemical standard.

Analytical protocol outline (general; adapt to your method):

• Preparation: Accurately weigh standard into a volumetric flask, add suitable solvent (e.g., MeCN or MeOH), dissolve fully, and bring to volume. If potency is provided on the CoA, correct the weighed amount accordingly.
• Calibration: Prepare a multi‑point curve spanning expected impurity levels (e.g., 0.02–0.5% relative to API), using either external calibration with this standard or relative response factors vs. alogliptin.
• Injection: Filter or centrifuge prior to LC injection. Maintain consistent injection solvent composition with initial mobile phase to avoid peak distortion.
• Documentation: Record batch/lot number, preparation date, solvent, concentration, and any observed instability.

For mass spectrometry, optimize source parameters and consider positive‑ion ESI for basic heterocycles (general guidance).

Biological Roles

This product is an analytical impurity standard and is not intended to elicit biological activity in laboratory studies. No intrinsic biological role is assigned.

Context (general):

• As a structurally related compound to alogliptin (a DPP‑4 inhibitor), some impurities can share motifs such as heteroaromatics and amines. However, impurity standards are supplied for analytical control and do not imply any biological function or potency.
• If used in exploratory assays, treat exclusively as a chemical control and follow institutional approval processes. Do not use for in vivo work or diagnostic purposes.

All work with this compound should be framed as research use only, focused on method development, identification, and quantification of related substances in drug substance/product matrices.

Buffer Applications

Not typically applicable. This item is a small‑molecule impurity standard rather than a buffering reagent.

Practical note for analysts:

• When deploying in LC or LC–MS workflows, select volatile buffers (e.g., ammonium formate/acetate, 2–20 mM) or formic acid (0.05–0.2%) as mobile‑phase modifiers to manage peak shape and ionization of basic heterocycles (general guidance). Optimize pH to control ionization and retention relative to alogliptin and its impurities.

Green Alternatives

Although this item is an impurity standard (not a process solvent), greener choices apply mainly to analytical solvent systems.

General greener substitutions (literature/practice; not item‑specific):

• Replace part of acetonitrile with ethanol or methanol where chromatographic selectivity permits. Methanol is generally considered greener than MeCN but increases backpressure.
• Consider water‑rich gradients and shorter columns with smaller particles/superficially porous materials to reduce solvent consumption without sacrificing resolution.
• Evaluate buffer strength minimization (e.g., 2–5 mM volatile buffers) compatible with MS to lower salt load and waste.

Small comparison (typical RP‑LC choices):

• MeCN vs MeOH: MeCN offers lower viscosity and faster runs; MeOH is greener but may require longer run times or higher temperatures to manage pressure.
• IPA as strong wash: effective for column cleanup; use sparingly due to higher environmental impact and viscosity.

Operational practices:

• Scale injections appropriately and optimize detection sensitivity to avoid unnecessary solvent‑intensive replicates.
• Use autosampler vial inserts to reduce solution volumes and solvent use.

Note: Selection must be validated for your specific method to maintain resolution of alogliptin and its impurities.

Pharmaceutical Uses

No therapeutic or clinical uses are claimed. Research/analytical use only.

Role in pharmaceutical quality control (general):

• Employed as a reference impurity standard for development and validation of assays per ICH Q2(R1) and qualification per ICH Q3A/B for drug substances/products containing alogliptin.
• Supports establishment of reporting/identification/qualification thresholds, response factors, and relative retention times in chromatographic methods.
• Used in system suitability testing (resolution, tailing factor, %RSD), specificity assessments in stability‑indicating methods, and forced degradation mapping of alogliptin.
• May be included in impurity mixes for routine lot release and ongoing stability monitoring.

Documentation:

• Maintain traceability to batch CoA, including purity on an as‑is basis and uncertainty where reported. Record storage and solution stability conditions used in validated methods.

Physical Properties

Item-specific physicochemical constants are not provided for this impurity standard.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting/boiling point: Not specified for this item; refer to CoA/Spec Sheet.
• Density/refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP, pKa: Not specified for this item; refer to CoA/Spec Sheet.

General guidance (literature/typical for alogliptin‑related impurities; not item‑specific):

• Many alogliptin impurities contain basic nitrogen atoms (piperidinyl or aminopyrimidinyl), which often afford good solubility in methanol, acetonitrile, and DMSO, and limited solubility in nonpolar hydrocarbons.
• For LC/LC–MS reference solutions, stock concentrations of 0.1–1.0 mg/mL in acetonitrile, methanol, or DMSO are commonly used, then diluted into water/organic mobile phase with 0.1% formic acid or 10–20 mM ammonium formate/acetate as needed (method‑dependent).

Note: For definitive physical data, UV cutoff, water content, and impurity limits, consult the item‑specific CoA/Spec Sheet and SDS.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Context for impurity/reference standards (general):

• Impurity standards are commonly supplied with a Certificate of Analysis (CoA) that details assay purity (by HPLC/UPLC), identity confirmation (NMR, HRMS, IR), and residual solvents/water. Where applicable, quantitative potency on an as‑is basis is reported to enable accurate mass balance in analytical methods.
• For chromatographic use, look for data on chromatographic purity, peak homogeneity, and counter‑ion/form (free base vs. salt), as these impact retention, MS response, and gravimetric accuracy.
• If a stabilizer is present or a specific solid form is used (amorphous/crystalline, solvate), it will be declared on the CoA. None is specified here.

What to expect with this item:

• As “Alogliptin Impurity 07,” this product is intended for research and analytical use (method development, validation, system suitability, and impurity profiling). For item‑specific limits such as water, residual solvents, and metal content: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

Primary use: analytical reference/impurity standard related to alogliptin. While not generally used as a reagent, it is valuable for:

• Method development and validation of alogliptin drug substance/product per ICH Q2/Q3 guidelines: establishing specificity, linearity, LOQ/LLOD, and accuracy for impurity assays.
• System suitability testing and peak identification in HPLC/UPLC–UV and LC–MS/MS methods, including relative retention time (RRT) assignment and MS fragmentation verification.
• Forced‑degradation and stability‑indicating studies to confirm separation of process/degradant peaks and to map degradation pathways of the parent API.
• Calibration as a single‑component standard or as part of an impurity mix to construct response factors (RF/RCF) when UV or MS responses differ from the parent.

Practical tips (general; not item‑specific):

• Prepare gravimetrically using potency‑corrected values from the CoA when available. Use Class A glassware; minimize hygroscopic uptake by working swiftly and closing containers promptly.
• Filter stock solutions (0.2 µm PTFE) before LC injection to protect columns; verify no adsorption losses.
• Track solution stability at room temperature and refrigerated conditions; record any conversion or additional peaks over time. Protect from light if chromophores are present.

Note: No specific synthetic reaction applications are claimed for this product.

Reaction Conditions

Not a reagent for chemical synthesis; typical “reaction conditions” do not apply. For analytical solution preparation and LC analysis (general guidance; not item‑specific):

• Stock solutions: 0.1–1.0 mg/mL in acetonitrile, methanol, or DMSO. Verify complete dissolution by gentle vortexing/sonication. Use amber vials if light sensitive.
• Working solutions: Dilute into mobile phase (e.g., water/MeCN or water/MeOH with 0.05–0.1% formic acid or 2–10 mM ammonium formate/acetate) to target method concentrations (e.g., 0.05–5 µg/mL for UV; lower for MS detection depending on response).
• Column chemistry: C18 or polar‑embedded RP phases are commonly used for alogliptin impurity separations; adjust organic and pH to resolve basic species. Temperature 25–40 °C can improve peak shape and reduce backpressure.
• Stability checks: Assess immediate and 24–48 h stability at autosampler temperature; document any additional peaks or potency drift. Prepare fresh solutions as needed.

Always adapt conditions to your validated method and consult the CoA for any solvent or stability notes specific to this item.

Safety and Handling

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H‑statements / pictograms: Not specified for this item; refer to SDS.

General laboratory precautions (good practice for small‑molecule impurity standards):

• Handle in a chemical fume hood; avoid inhalation of dust or vapors and contact with skin/eyes. Wear lab coat, safety glasses, and appropriate chemical‑resistant gloves.
• Prevent cross‑contamination of reference standards. Use clean, dedicated spatulas and certified volumetric ware for solution prep.
• Avoid incompatible reagents typical for organic amines/heteroaromatics (strong oxidizers). Verify incompatibilities in the SDS once available.
• First aid (overview; defer to SDS): In case of eye/skin contact, rinse with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical attention. Provide SDS to responders.
• Waste: Collect solutions and residues in labeled organic waste containers; dispose of according to institutional and local regulations.
• Transport and storage conditions are typically non‑hazardous for analytical quantities, but always defer to the product’s SDS for authoritative guidance.

Solvent Selection

Item‑specific solubility is not provided; select solvents empirically while considering analytical objectives.

General guidance for alogliptin‑related impurities (literature/experience; not item‑specific):

• Likely polarity: moderately polar, often bearing one or more basic nitrogens.
• Useful stock solvents: Acetonitrile (MeCN), methanol (MeOH), and DMSO for primary dissolution; further dilution into water/MeCN or water/MeOH mobile phases is typical.
• LC–MS compatibility: MeCN and MeOH are preferred. Aqueous buffers such as ammonium formate/acetate (2–20 mM) with or without 0.1% formic acid are commonly used.
• Avoid highly protic, strongly basic, or strongly acidic media unless method‑directed, to minimize degradation or salt‑form shifts.

Quick comparison (general):

• MeCN: low viscosity, strong eluotropic strength in RP‑LC, excellent MS performance.
• MeOH: greener profile, higher viscosity, different selectivity (can improve resolution of closely eluting impurities).
• DMSO: strong solvency for difficult solids; keep final DMSO ≤1–2% in injection solutions to protect columns and maintain peak shape.

Note: Confirm actual solubility and stability for this item by small‑scale tests and consult the CoA for any solvent restrictions if provided.

Storage and Reconstitution

• Storage conditions (item‑specific): Room temperature (per product data). Keep container tightly closed.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

Best practices (general; not item‑specific):

• Store in a dry, inert environment (desiccator with desiccant) and protect from light to minimize potential degradation of heteroaromatic amines.
• After opening, promptly re‑cap and purge headspace with dry nitrogen if available. Record first‑open date.
• For solution stocks, prepare small aliquots in amber vials to minimize freeze–thaw and headspace oxygen. Short‑term storage at 2–8 °C and longer‑term at −20 °C is common for analytical solutions; validate stability for your method.
• Reconstitution: If provided as a solid, dissolve in acetonitrile, methanol, or DMSO to prepare a primary concentrate, then dilute with mobile phase as required. Filter if needed.

Shelf life and specific stability limits, water content, and residual solvent details: Not specified for this item; refer to CoA/Spec Sheet.

Research Use Note: For research use only.

Structure and Identity

• Item name: Alogliptin Impurity 07 (reference/impurity standard related to the DPP‑4 inhibitor alogliptin)
• CAS: 1618644-29-3
• CID: 70306796
• InChIKey: 326158 (identifier as provided; full-length InChIKey not specified for this item; refer to CoA/Spec Sheet)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general context):

• This product is supplied as an impurity standard structurally related to alogliptin (a cyanobenzylated aminopiperidine–fused heteroaromatic scaffold; general knowledge), but the exact substitution pattern and stereochemical details for “Impurity 07” are not specified in the provided item data.
• 2D description: Without a provided structure, a precise atom‑level description cannot be given. Expect heteroaromatic and basic amine motifs typical of alogliptin‑related species (literature, general). Confirm exact features from the item’s CoA/Spec Sheet and accompanying structure file when provided.

Synthetic Utility

This product is supplied as an impurity standard and is not typically used as a synthetic reagent. Nevertheless, in research settings:

• It can serve as a marker compound for studying degradation pathways and mechanistic transformations of alogliptin under stress conditions (acid/base, oxidative, photolytic, thermal), aiding in hypothesizing reaction routes (e.g., dealkylation, ring opening, N‑oxidation) based on observed formation of the impurity.
• If the structure is disclosed in the CoA/Spec Sheet, it may inform retrosynthetic analysis towards process improvements by identifying steps likely to generate this impurity and suggesting orthogonal protection or milder conditions.
• Fragmentation patterns obtained by HRMS/MS and comparison to this standard help assign structures to unknowns in synthetic streams.

Note: No item‑specific functional group reactivity, protecting group behavior, or named reaction utility is stated because the exact structure and substituent pattern for “Alogliptin Impurity 07” are not provided in the current item data.

Target Specificity

Not applicable. This is a small‑molecule impurity standard and does not possess “target specificity” in the sense used for biologicals (antibodies, enzymes, or inhibitors within an assay panel). No antigen/epitope/clone/isotype data are relevant.